1,3-Cyclohexanedione → Mesotrione

HRID 324721Notes

Reaction equation

HRID 324721 reaction equation
[N+:1]([C:4]1[CH:16]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:14]=[CH:13][C:5]=1[C:6](N1C=NC=N1)=[O:7])([O-:3])=[O:2].[C:21]1(=[O:28])[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:16]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:14]=[CH:13][C:5]=1[C:6]([CH:22]1[C:23](=[O:27])[CH2:24][CH2:25][CH2:26][C:21]1=[O:28])=[O:7])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 11430Potassium CarbonateHCID 22005920HCID 22005920, compound

Product 1

HCID 175967MesotrioneYield 103.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Nitro-4-methanesulphonylbenzoyl)-1,2,4-triazole (666 mg), cyclohexan-1,3-dione (254 mg) and potassium carbonate (419 mg, 1.8 mmol, 1.4 equiv) were suspended in acetonitrile (30 ml) and stirred overnight. The acetonitrile was removed under reduced pressure, the residue dissolved in water (100 ml) and acidified with 1 M hydrogen chloride solution to pH 1.5. The solution was extracted with dichloromethane, dried (magnesium sulfate), filtered and the solvent removed under reduced pressure to afford the title compound as a pale yellow solid (0.789g, quant).

Workup

  1. customThe acetonitrile was removed under reduced pressure
  2. dissolutionthe residue dissolved in water (100 ml)
  3. extractionThe solution was extracted with dichloromethane
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-0d76cd9e5abd47e2a6fb68556f6bfd6c
Source dataset
uspto-grants-2001_04
Patent number
US06218579B1

Reaction notes

Loading…